Molecules 2007, 12(5), 1035-1044; doi:10.3390/12051035
Article

Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity

Charles Mutai 1 email, Dennis Abatis 1 email, Constantinos Vagias 1,* email, Dimitri Moreau 3 email, Christos Roussakis 3 email and Vassilios Roussis 1 email
1 University of Athens, Department of Pharmacy, Division of Pharmacognosy and Chemistry of Natural Products, Panepistimiopolis Zografou, Athens 157 71, Greece 2 Kenya Medical Research Institute, Centre for Traditional Medicine and Drug Research, P.O Box 54840, Nairobi, Kenya 3 ISOMer, Laboratoire de Pharmacogénomique Marine, Faculté de Pharmacie, 1 Rue Gaston Veil, F-44035 Nantes, France
* Author to whom correspondence should be addressed.
Received: 7 April 2007; in revised form: 12 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
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Abstract: Three new pentacyclic triterpenoids: (20R)-3-oxolupan-30-al (1), (20S)-3-oxolupan-30-al (2) and (20R)-28-hydroxylupen-30-al-3-one (3), along with (20S)-3β-hydroxylupan-30-al (4), the latter previously described as a constituent of an epimeric mixture, were isolated from Acacia mellifera. In addition, the known metabolites 30-hydroxylup-20-(29)-en-3-one (5), 30-hydroxylup-20-(29)-en-3β-ol (6), atranorin, methyl 2,4-dihydroxy-3,6 dimethyl benzoate, sitosterol-3β-O-glucoside and linoleic acid were found in the analyzed plant species for the first time. The structures of the new metabolites were elucidated by extensive spectroscopic analyses and their relative stereochemistry was determined by NOESY experiments. The new metabolite 3 exhibited significant cytotoxic activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.
Keywords: Acacia mellifera; lupanes; cytotoxicity; NSCLC-N6 cell line; (20R)-28-hydroxylupen-30-al-3-one; (20R)-3-oxolupan-30-al; (20S)-3-oxolupan-30-al

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MDPI and ACS Style

Mutai, C.; Abatis, D.; Vagias, C.; Moreau, D.; Roussakis, C.; Roussis, V. Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity. Molecules 2007, 12, 1035-1044.

AMA Style

Mutai C, Abatis D, Vagias C, Moreau D, Roussakis C, Roussis V. Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity. Molecules. 2007; 12(5):1035-1044.

Chicago/Turabian Style

Mutai, Charles; Abatis, Dennis; Vagias, Constantinos; Moreau, Dimitri; Roussakis, Christos; Roussis, Vassilios. 2007. "Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity." Molecules 12, no. 5: 1035-1044.

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